5-(Aminomethyl)-1-benzyl-5-phenyl-pyrrolidin-2-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-(Aminomethyl)-1-benzyl-5-phenyl-pyrrolidin-2-one
• 英文别名: 5-(aminomethyl)-1-benzyl-5-phenylpyrrolidin-2-one
• 化学式: C₁₈H₂₀N₂O
• 分子量: 280.37
• InChiKey: XXFKTZZXQHPADP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(N-苄基氨基)-2-苯基乙腈 在 sodium tetrahydroborate 、 cobalt(II) chloride hexahydrate 、 苄基三乙基氯化铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 4.0h， 生成 5-(Aminomethyl)-1-benzyl-5-phenyl-pyrrolidin-2-one
  参考文献：
  名称：

  Anti-human immunodeficiency activity of novel 2-arylpyrrolidine analogs

  摘要：

  A series of 26 new compounds were synthesized and screened for their anti-human immunodeficiency virus-1 and cytotoxicity activity. Of these, 14 were found to be inhibitors of human immunodeficiency virus replications in primary human lymphocytes with 50 % effective concentration values < 20 A mu M. Moreover, most of the compounds were cytotoxic to human lymphocytes, CEM, and Vero cells. Our structure activity relationship study identified different patterns. Compounds 2g-j and 4 (whose structure is closer to the loviride structure) were very potent. Comparing the activity of the compounds containing the 2-aryl substituents, we observed that compounds with benzyloxyphenyl groups were more potent. Compounds in which the 1-aryl moiety contained methyl group in 4- or 3,5-positions also showed high activity. In the series of compounds containing the nitrile, amine, and amide groups, we observed a decrease in activity with CN > NH2 > C(O)NH2. The difference of activity between the 5-membered and 4-membered rings compounds was not significant. This initial information could be used to design improved anti-human immunodeficiency virus compounds in this class.

  DOI：

  10.1007/s00044-016-1731-7

文献信息

• Design, antihuman immunodeficiency activity and molecular docking studies of synthesized 2-aryl and 2-pyrimidinyl pyrrolidines
  作者：Sahak P. Gasparyan、Ashot H. Martirosyan、Marina V. Alexanyan、Gohar K. Harutyunyan、Garri V. Chilingaryan、Steve Coats、Raymond F. Schinazi

  DOI：10.1007/s11030-020-10095-1

  日期：2021.11

  different patterns. In the series of 2-aryl pyrrolidines, comparing the activity of the compounds containing 2-aryl substituents we observed that compounds 1c, 1f-j, 2f,g with benzyloxyphenyl and isopropoxy groups were more potent. Compounds 1g-j, 2f,g, in which the 1-aryl moiety contained a methyl group in 3,5- or 4-positions also showed high activity. In the series of compounds containing the amide

  合成了一系列三十一种新化合物，并评估了它们的抗 HIV-1 和细胞毒性活性。其中，12 个被发现是人类原代淋巴细胞中 HIV 复制的抑制剂，中位有效浓度 (EC50) 值 < 20 µM。然而，大多数化合物在不同细胞中表现出细胞毒性。我们的结构活性关系研究确定了不同的模式。在 2-芳基吡咯烷系列中，比较含有 2-芳基取代基的化合物的活性，我们观察到具有苄氧基苯基和异丙氧基的化合物 1c、1f-j、2f、g 更有效。其中 1-芳基部分在 3,5-或 4-位含有甲基的化合物 1g-j、2f,g 也显示出高活性。在含有酰胺的系列化合物中，氨基甲基和腈基团我们观察到 C(O)NH2 < CH2NH2 < CN 的活性增加。在 2-嘧啶基吡咯烷系列中，衍生物 5e 和 5f 证明了最好的结果，其中在嘧啶环的第 1 位存在苄基片段，在第 6 位存在苯胺片段，我们观察到抗 HIV 活性增加。对合成的化合物与